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Mechanisms of the Formation of Nonvolatile and Volatile Oxidation Products from Methyl Linoleic Acid at High Temperatures

Yunping Yao, Tianliang Wang, Zhiyuan Qiang, Wenqi Du, Changmo Li

2023Journal of Agricultural and Food Chemistry23 citationsDOI

Abstract

The impact of the oxidation of linoleic acid cannot be overlooked in daily food consumption. This study used gas chromatography-mass spectrometry (GC-MS) to identify both nonvolatile oxidation products and volatile oxidation products of methyl linoleic acid at 180 °C and density function theory to investigate oxidation mechanisms. An analysis of nonvolatile oxidation products revealed the presence of three primary oxidation products. The three primary oxidation products were identified as hydroperoxides, peroxide-linked dimers, and heterocyclic compounds in a ratio of 2.70:1:3.69 (mmol/mmol/mmol). The volatile components of secondary oxidation products were found including aldehydes (40.77%), alkanes (19.89%), alcohols (9.02%), furans (6.11%), epoxides (0.46%), and acids (2.50%). DFT calculation proved that the secondary oxidation products mainly came from peroxides (77%). Finally, we look forward to our research contributing positively to lipid autoxidation and human health.

Topics & Concepts

AutoxidationChemistryLinoleic acidPeroxideLipid oxidationOrganic chemistryPrimary (astronomy)Mass spectrometryGas chromatographyChromatographyAntioxidantFatty acidPhysicsAstronomyFree Radicals and AntioxidantsEdible Oils Quality and AnalysisMeat and Animal Product Quality
Mechanisms of the Formation of Nonvolatile and Volatile Oxidation Products from Methyl Linoleic Acid at High Temperatures | Litcius